The LiveCity Project addresses a number of communities where the citizens of a city can have specific challenges and derive immediate benefits or advantages from the proper and effective use of live interactive high definition video-to-video (v2v) communications over the Internet, for various sectors of applications and/or related services. One of these communities is the educational community, where major benefits and impacts may raise, as a result of the innovative v2v implementation and use, to support teaching and learning activities. In this paper, we propose a specific context to satisfy this challenge, based on the formation of a “network” of involved schools, where we also identify essential users’ needs and propose distinct educational use cases (i.e.: v2v for school-to-school communication and v2v for an interactive homework channel). In addition, we discuss potential benefits from this action and we identify legal and ethical issues that may affect further progress.